Month: September 2021

Application of 6973-09-7, A common heterocyclic compound, 6973-09-7, name is 5-Amino-2-methylbenzenesulfonamide, molecular formula is C7H10N2O2S, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred suspension of the product of Intermediate Example 4 (1.1 g, 3.7 mmol) in 10 mL of THF, was added 5-amino-2-methylbenzenesulfonamide (0.70 g, 3.8 mmol, 1.0 equiv) at room temperature. The reaction mixture was heated at reflux for 3 h, then 4 M HCI in 1 ,4-dioxane (18 muL, 0.072 mmol) was added in one portion. After 5 h, the suspension was cooled to room temperature, and filtered. The resulting solid was washed with 16 mL of THF and dried in the air to yield 1.6 g (92%) of 5-({4- [(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl}amino)-2-methylbenzene sulfonamide monohydrochloride as a light yellow solid.

The synthetic route of 6973-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/64753; (2007); A2;,
Amide – Wikipedia,
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Related Products of 2895-21-8, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 2895-21-8, name is N-Isopropyl-2-chloroacetamide, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 4-{[6-(3-chlorophenyl)-4-oxo-4,5-dihydropyrazolo[1 ,5-a]pyrazin-2-yl]oxy}butyl acetate (0.25 g, P23) and potassium carbonate (0.18 g) in dry acetonitrile (6 ml.) 2-chloro- N-(1-methylethyl)acetamide (0.1 g) was added and the reaction was stirred at 8O0C on. After cooling the mixture was diluted with AcOEt and washed with chilly water and brine. The organic phase was dried, filtered and the solvent evaporated under vacuum. The crude was dissolved in THF (20 ml_), lithium hydroxyde (5 ml_, 0.5 M solution in water) was added and the mixture was stirred at RT for 2h. Solvent was removed under reduced pressure; the residue was taken up with AcOEt and washed with water. The organic phase was dried, filtered and evaporated under vacuum to give a mixture of the title compounds (0.21 g) that was used in next step without further purification.MS ( m/z): 433 [MH]+.

The chemical industry reduces the impact on the environment during synthesis N-Isopropyl-2-chloroacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/130232; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., 57561-39-4

A 100 mL round-bottomed flask (rbf) equipped with a magnetic stirbar was charged withTHF (15 mL), water (15 mL) and 2-(methylamino)ethanol (2.00 mL, 25.0 mmol). To thestirred solution exposed to air Boc2O (5.9 g, 27 mmol) was added in 4 portions within 10min resulting in gas evolution. Several drops of sat. aq. NaHCO3 were added 40 min laterto keep the pH around 8. Most of THF was removed on a rotary evaporator 4.5 h after theBoc2O addition. The residue was transferred into a separatory funnel using EtOAc,washed with aq. 2.5 M NH4Cl (20 mL) and brine. The organic phase was dried overMgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporator.Using hexane transferred the crude product into a pre-weighed 100 mL rbf, removedvolatiles on the rotary evaporator (20 mm Hg). N-Methyl-N-Boc-aminoethanol wasobtained as colorless oil: 4.26 g (97%). A 3-neck rbf equipped with a magnetic stirbar, arubber septum, a glass stopcock (Teflon tape, central neck) and connected to a vacuumline was charged with 4.26 g of the protected amine (24.3 mmol). After evacuation andrefill with nitrogen 90 mL of THF freshly distilled from sodium-benzophenone ketyl wasadded. The flask was placed in an ice-water bath. Approx. 25 min later quickly added1.09 g of 60% NaH (27.2 mmol) in paraffin via the central neck. Approx. 20 min lateradded allyl bromide (2.15 mL, 24.8 mmol) with a syringe via the rubber septum followedby 0.4487 g of tetrabutylammonium iodide (1.21 mmol, 5 mol%) via the central neck.Approx. 2.5 h later removed the cold bath and let the reaction mixture stirring for 16 hunder nitrogen. The flask was immersed in ice-water bath followed by careful addition ofwater (20 mL, audible sound). The mixture was transferred into a 250 mL separatoryfunnel followed by addition of EtOAc (50 mL) and extraction. The organic phase was setaside and the aqueous phase was extracted with fresh portion of EtOAc (40 mL). Theorganic phases were combined, washed with aq. 2.5 M NH4Cl (50 mL) and brine, driedover MgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporatorleaving behind yellow oil, which was chromatographed on silica (normal phase, EtOAchexane,1:3) furnishing 3.7916 g of N-Methyl-N-Boc-aminoethanol O-allyl ether ascolorless oil (72% yield). N-Boc deprotection was achieved according to the method ofStrazzolini et al.1 To a 200 mL rbf charged with a magnetic stirbar and CH2Cl2 (22 mL)and immersed in an ice-water bath added 1.48 mL of conc. H2SO4 (assumed to be 17.9 M,26.5 mmol) with stirring. The central neck was plugged with a glass stopcock while adropping funnel was attached to the side-neck. A solution of 3.79 g of N-Methyl-N-BocaminoethanolO-allyl ether (17.6 mmol) in 65 mL CH2Cl2 was added to the solution ofacid dropwise from the addition funnel within 45 min followed by removal of cold bathand stirring at rt for 6 h. The dark purple mixture was transferred into a separatory funneland extracted with water (40 mL). The organic phase was extracted with additional 40mL of water, after which the aqueous extracts were combined in a 200 mL Erlenmeyerflask and basified by addition of NaOH (3.245 g in 15 mL water) with stirring. Theresulting solution was saturated with NaCl and extracted with three 50 mL portions ofCH2Cl2. Combined extracts were dried over Na2SO4, filtered into a 500 mL rbf andstripped of the solvent on the rotary evaporator (200 mm Hg). The resulting yellowish oilwas fractionated in vacuo using a one-piece distillation head and a receiving flask held at-50 C. The title compound was obtained as colorless oil (1.2208 g, 60% yield).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kultyshev, Roman G.; Miyazawa, Akira; Tetrahedron; vol. 67; 11; (2011); p. 2139 – 2148;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2886-65-9, name is 7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

EXAMPLE 3 Preparation of 10-chloro-11b-(2-fluorophenyl)-2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6-(7H)-one SPC17 To 15 g. (51.9 mmole) of 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 150 ml. of dry benzene, 9 g. (67.7 mmole) of aluminum chloride was added and stirring was continued 15 minutes. The reaction mixture was cooled in an ice bath and 8.8 g. (0.2 mole) of ethylene oxide was added dropwise. After 18 hours of stirring at room temperature, the reaction mixture was heated to 40 for 1 hour and then cooled to room temperature and treated with 5 g. (37.6 mmole) of aluminum chloride, followed by 4.4 g. (0.1 mole) of ethylene oxide. The reaction mixture was heated 4 hours at 45-50 and then evaporated to dryness. ethylene chloride, ice and ammonium hydroxide were added and the solid removed by filtration. The filtrate was separated and the organic phase reduced to dryness in vacuo. The residue was dissolved in dilute hydrochloric acid and the pH of the solution adjusted to 5 with ammonium hydroxide. The acidic solution was washed with ether, made basic and extracted with methylene chloride. The organic phase was washed with brine, dried and evaporated to dryness. Recrystallization from methylene chloride-hexane gave the above-titled product as colorless rods, m.p. 183-184.

The synthetic route of 2886-65-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US3965151; (1976); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: amides-buliding-blocks

The Schiff base HL1 was synthesized with a method differentfrom the one in the literature [24], by refluxing sulfacetamide(1 mmol, 0.214 g) and salicylaldehyde (1 mmol, 0.122 g) in about15 ml of methanol for 3 h at ca.70 C, in the presence of 4-5 dropsof conc. H2SO4. The solid product was collected through filtrationand finally air dried. Yield: 58%. M.P. = 215 C. Anal. Calcd. forC15H14N2O4S (%):C, 56.59; H, 4.43; N, 8.80. Found: C, 56.42; H,4.25; N, 8.75. FT-IR (KBr, cm1): mmax cm1 (KBr):1645 (s, CN),1715 (CO), 1575, 1616 (CCaromatic), 1093, 1157 (SO2) 3340(NAH). UV-vis: kmax (nm) (e, M1 cm1) (DMSO-d6): 350(40,000), 320 (41,000). 1H NMR (DMSO-d6, 400 MHz):6-8 (m, 8H), 9 (s, 1H), 10 (s, 1H), 3 (s, 3H), 11 (s, 1H).

The synthetic route of N-((4-Aminophenyl)sulfonyl)acetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Salehi, Mehdi; Ghasemi, Fateme; Kubicki, Maciej; Asadi, Asadollah; Behzad, Mahdi; Ghasemi, Mohammad Hadi; Gholizadeh, Ahmad; Inorganica Chimica Acta; vol. 453; (2016); p. 238 – 246;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 27466-83-7, name is 4-Bromo-N-methylbenzamide, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 27466-83-7, Computed Properties of C8H8BrNO

General procedure: To a dried screw-capped vial were added benzamide 2 (0.10mmol), ethyl acrylate 3 (0.15mmol), 1b (4.8mg, 0.01mmol), AgSbF6 (6.8mg, 0.02mmol), AgOAc (41.7mg, 0.25mmol), and 1,2-dichloroethane (1.0mL) under Ar atmosphere. The vial was capped and the mixture was heated at 60C for 13h with stirring. After the mixture was cooled to room temperature, saturated EDTA·2Na aqwas added following dilution with CH2Cl2. Organic layer was separated and aqueous layer was extracted with CH2Cl2 (×2). Combined organic layers were dried over Na2SO4. After filtration and evaporation, obtained crude mixture was purified by silica gel column chromatography (CH2Cl2/EtOAc) to give product3.4.1.1 _4.1.5 (E)-Ethyl 3-(5-bromo-2-(methylcarbamoyl)phenyl)acrylate (4e) A colorless solid; IR (KBr) nu 3079, 2975, 2935, 1719, 1642, 1561, 1316, 1190, 1032, 979, 862 cm-1; 1H NMR (CDCl3, 400 MHz) delta 1.32 (t, J=7.5 Hz, 3H), 3.00 (d, J=5.2 Hz, 3H), 4.23 (q, J=7.5 Hz, 2H), 5.88 (br s, 1H), 6.36 (d, J=16.0 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 7.49 (d, J=8.6 Hz, 1H), 7.74 (s, 1H), 7.90 (d, J=16.0 Hz, 1H); 13C NMR (CDCl3, 100 MHz) delta 14.4, 27.1, 60.1, 122.1, 124.1, 124.7, 129.3, 130.1, 132.7, 134.9, 135.8, 140.5, 166.2, 168.5; HRMS (ESI): m/z calculated for [M+Na]+: 334.0049, found: 334.0050.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Suzuki, Yudai; Sun, Bo; Yoshino, Tatsuhiko; Kanai, Motomu; Matsunaga, Shigeki; Tetrahedron; vol. 71; 26-27; (2015); p. 4552 – 4556;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 194920-62-2, name is tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate, A new synthetic method of this compound is introduced below., Recommanded Product: tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)carbamate

In four flasks (20mL), compound IX (0.45mmol in each) was dissolved in DMF (5mL in each) and afterwards, compounds I, II, V, or VI (2mmol), HOAt (3mmol), PyAOP (2mmol) and DIPEA (8mmol), were added to each flask. The reaction mixture of each flask was heated at 100C for 12h, diluted with water and extracted three times with DCM. Each organic layer was dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. Finally, each residue was purified by column chromatography using hexane/ethyl acetate as the solvent and thus compounds 5 (94%), 6 (91%), 7 (86%), or 8 (90%) were yielded, respectively.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Medina-O’Donnell, Marta; Rivas, Francisco; Reyes-Zurita, Fernando J.; Martinez, Antonio; Martin-Fonseca, Samuel; Garcia-Granados, Andres; Ferrer-Martin, Rosa M.; Lupianez, Jose A.; Parra, Andres; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 64 – 78;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37045-73-1, name is 3-(Methylsulfonamido)aniline, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 37045-73-1, Application In Synthesis of 3-(Methylsulfonamido)aniline

Under nitrogen or argon, 0.4 mmol, 0.2mmol, Ir(ppy) 3(2mg) and DMF1 ml was added to the reaction flask, followed by blue LED lights(7W) at room temperature irradiation straight trivalent iodine reagent completeconversion of the reaction. Add 10 ml of saturated Na 2CO 3Aqueous solution, andextracted three times with ethyl acetate, the organic layer was washed with water andonce with saturated brine, dried over anhydrous Na 2SO 4The organic layer was dried.Column chromatography (eluent: petroleum ether 60-90: ethyl acetate = 10: 1-5: 1) to Ethyl acetate = 10: 1-5: 1) to give the product , S; Yield 43%.Rate of 19%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Nanjing University; Zhu, ChengJian; Xie, jin; Xu, Pan; (13 pag.)CN103553857; (2016); B;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 53844-02-3,Some common heterocyclic compound, 53844-02-3, name is Benzyl (2-bromoethyl)carbamate, molecular formula is C10H12BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Treat a -78 C solution of diisopropylamine (35 g, 0.346 mol) in THF (300 mL), under N2, drop-wise with a solution of n-butyllithium (2.5 M, 127 mL, 0.317 mol), warm to -30 C for 0.5 h, re-cool to -78C and treat drop-wise with a solution of isobutyronitrile (19.9 g, 0.288 mol) in THF (100 mL). Stir the mixture at -78C for 0.5 h, treat with a solution of benzyl (2-bromoethyl)carbamate (74 g, 0.288 mol) in THF (100 mL), stir at – 78C for 1 h, then warm to RT and stir overnight. Treat the mixture with H20, separate the layers, extract the aqueous layer with EtOAc, wash the combined organics with brine, dry over Na2S04, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (15 g, 21 % yield). MS (m/z): 247.2 (M+l).

The synthetic route of 53844-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DECIPHERA PHARMACEUTICALS, LLC; ELI LILLY AND COMPANY; FLYNN, Daniel L.; KAUFMAN, Michael D.; VOGETI, Lakshminarayana; WISE, Scott C.; LU, Wei-Ping; SMITH, Bryan D.; CALDWELL, Timothy M.; PATT, William C.; HENRY, James Robert; HIPSKIND, Philip Arthur; PENG, Sheng-Bin; WO2013/134298; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 120157-96-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 120157-96-2, name is Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To a solution of the compound obtained in the above step (1) (1.5 g) in tetrahydrofuran (15 mL) was added 60 % oily dispersion of sodium hydride (407 mg) under ice-cooling and the mixture was stirred at room temperature for 30 minutes. Thereto was added dropwise ethyl iodide (2.26 mL) under ice-cooling and the mixture was stirred at 60 C for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (10 mL) and thereto was added water (20 mL). After stirring, the organic layer was separated and concentrated and the resultant residue was purified by a flash column chromatography on NH-silica gel (Solvent; n-hexane/ethyl acetate = 20: 1) to give methyl 4-[[N-ethyl-N-(tert-butoxycarbonyl)]aminomethyl]benzoate (929 mg, yield: 56 %) as an amorphous solid. MS(APCI)m/z; 294 [M+H]+

The synthetic route of Methyl 4-(((tert-butoxycarbonyl)amino)methyl)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TANABE SEIYAKU CO., LTD.; EP1772454; (2007); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics